Trifluoroacetic acid → HCID 56967632, compound

Participants

Reaction Steps

To a stirred solution of the product of Step 2 (2.77 g, 5.46 mmol) in DCM (28 mL) was added TFA (28 mL). The resulting solution was stirred for 1 hour at room temperature. Heptanes were then added, and the mixture was concentrated in vacuo, azeotroping with DCM and heptanes until a constant weight was achieved. The resulting oil was taken up into acetonitrile (28 mL), and ammonium hydroxide (28 mL) was added. The solution was stirred at ambient temperature for approximately 5 minutes, then the reaction mixture was scratched with a glass pipette in order to promote crystallization. The reaction mixture was stirred for approximately 19 hours before being heated at 50° C. for 1 hour. The reaction mixture was cooled, and diluted with water (28 mL). The solids were filtered and the filter cake was rinsed with water and dried under high vacuum until constant weight was achieved to afford the desired product as an off-white solid. LRMS calc'd for C21H24N5O2 [M+H]+, 378; found 378. 1H NMR (500 MHz, DMSO-D6) δ 11.6 (s, 1H), 8.06 (s, 1H), 7.40-7.28 (br m, 5H), 7.10 (s, 1H), 6.52 (s, 1H), 5.13-5.07 (m, 2H), 4.61 (br s, 1H), 4.32 (br s, 1H), 3.98-3.64 (br m, 3H), 2.98-2.80 (m, 1H), 2.36-2.12 (br m, 2H), 2.04 (br m, 1H), 1.64 (br m, 1H), 1.50-1.22 (br m, 2H). Jak1 activity: ++.

Provenance & Evidence